Amination of the Baylis–Hillman Acetates in Ethanol

Regio- and Stereoselective Synthesis of α,β-dehydro-β-amino Esters

“…11 Hence, the development of various methodologies for the esters has been disclosed. [12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28]7 Among these protocols, using readily available Baylis-Hillman adducts as substrates provide a practical and straightforward choice. However, many suffer from long reaction times, low regioselectivity and low yields, the basic conditions, and the use of harmful solvents.…”

Facile Synthesis of Dihydroquinolines via Palladium Catalyzed Sequential Amination and Cyclisation of Morita‐Baylis‐Hillman Alcohols

“…The classical reactions including Knorr, [5] Friedlander, [6] Combes, [7] Skraup, [8] Niementowski, [9] Pfitzinger [10] and Deobner-von Miller [11] reactions have been frequently used for the preparation of Quinoline backbone. In spite of these methods, various transition metal (Fe, [12] Cu, [13] Rh, [14] Pd [15] and Au [16] etc) mediated annulations approaches are also been utilized towards the synthesis of this particular class of heterocyclic compounds. Among these, base catalyzed and/or transition metal catalyzed cyclizations of easily accessible Morita-Baylis-Hillman (MBH) adducts/acetates have received special attention in recent years.…”

“…[20] Napoleon and Manheri described an interesting synthetic route to N-substituted 1, 2-dihydroquinolines by adopting a tandem S N 2-S N Ar cyclization of MBH acetates in presence of alkyl or aryl amines. [21] Moreover, Palladium catalyzed synthesis of dihydroquinolines from MBH acetates by following substitution/CN coupling reaction, [22] Heck type reaction [23] and domino Heck reaction-cyclization pathways [24][25][26] are also described.…”

“…Reaction of 1 a with p-chloro substituted tosylamine (2 b) offered 3 g in 85 % yield ( Table 3, entry 10). Amination/cyclization of 1 a with aryl amines (2 c-f) also worked well forming the corresponding products 3 h-l in moderate to good yields (Table 3, entry [11][12][13][14][15]. However, the reactions using aliphatic amines 2 h and 2 i gave poor results (Table 3, entry [16][17].…”

Palladium-Catalyzed Arylic/Allylic Aminations: Permutable Domino Sequences for the Synthesis of Dihydroquinolines from Morita–Baylis–Hillman Adducts

“…Consequently, a number of strategies have been developed for the synthesis of these scaffolds including transition-metal- or organo-catalyzed reactions, as well as one-pot approaches from Morita–Baylis–Hillman (MBH) adducts. Indeed, the use of functionalized adducts derived from the MBH reaction is a convenient synthetic approach for the construction of various quinoline derivatives. , However, to the best of our knowledge, there are no reports concerning their one-pot synthesis directly from MBH alcohol adducts …”